Apartment holiday rentals in Sag Harbor

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Top-rated apartment rentals in Sag Harbor

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Guest favourite

Flat in Sag Harbor

4.84 out of 5 average rating, 172 reviews

Pet friendly artists apartment & cabin with sauna

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach, pet friendly beaches are even closer. Centrally located for easy commutes to all towns and even ocean beaches. Free bikes, surf boards, 3 stand up paddle boards and 2 canoes. Life vests for you and pets A large tick free, shaded, shaded dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. WIFI AC and heat but No bathroom!.

Guest favourite

Flat in Montauk

4.99 out of 5 average rating, 169 reviews

Duffy's on Lake Montauk 2

These newly renovated units are located on Lake Montauk, five minute drive from town and the ocean beaches. The property offers paddle boards, kayaks and beach chairs. There is a BBQ grill, a fire pit to enjoy sunsets and lounge chairs lake front to relax. The unit has a full kitchen, washer/dryer, queen bed, small living area, large screen TV and wifi. The units sit at a 90 degree angle to the lake with partial lake views from the deck. PRICES INCLUDE SUFFOLK COUNTY SALES AND OCCUPANCY TAX

Guest favourite

Flat in Sag Harbor

4.92 out of 5 average rating, 134 reviews

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

Guest favourite

Flat in Milford

4.97 out of 5 average rating, 518 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Guest favourite

Flat in Sag Harbor

4.96 out of 5 average rating, 133 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Guest favourite

Flat in Hampton Bays

4.96 out of 5 average rating, 269 reviews

The House of the Mermaid aka La Casa della Sirena

Welcome to The House of the Mermaid! Come stay in this newly renovated and decorated basement apartment in my house in a quiet and residential area of Hampton Bays. Close to all that you could ever want; restaurants, bars, shopping, and beaches. Perfect getaway for any season. The Hamptons are known for their amazing Summers at the beach, but don't forget about all that Long Island has to offer throughout the seasons. Shopping at Tanger Outlets, apple/pumpkin picking, and the N.F. vineyards!

Guest favourite

Flat in Sag Harbor

4.99 out of 5 average rating, 135 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Guest favourite

Flat in Hampton Bays

4.97 out of 5 average rating, 341 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

Guest favourite

Flat in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

Guest favourite

Flat in Sag Harbor

4.88 out of 5 average rating, 135 reviews

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 10 minute walk to historic Sag Harbor Village Main Street. Five minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea kettle. No pets - owner is allergic. No infants/children.

Guest favourite

Flat in Montauk

4.91 out of 5 average rating, 202 reviews

Montauk Beach Bungalow West

Inquire about discounts for monthly bookings. Charming, clean, private, quiet, 2 bed one bath ocean view apartment 500 feet from door to ocean beach through lovely dunes. Dine inside or out with view of the moon rising over the breaking waves. Includes BBQ and fire pit. Full kitchen with stove, oven, fridge, sink, coffee maker, toaster, microwave, pots pans dishes etc. -

Guest favourite

Flat in Southampton

4.96 out of 5 average rating, 169 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive